CN112521620B - Supramolecular phosphorescent probe reagent for sulfadimidine detection and preparation method thereof - Google Patents

Supramolecular phosphorescent probe reagent for sulfadimidine detection and preparation method thereof Download PDF

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CN112521620B
CN112521620B CN202011409494.0A CN202011409494A CN112521620B CN 112521620 B CN112521620 B CN 112521620B CN 202011409494 A CN202011409494 A CN 202011409494A CN 112521620 B CN112521620 B CN 112521620B
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sulfadimidine
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刘育
徐德奥
张瀛溟
王丽华
代现银
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Nankai University
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Abstract

A supramolecular phosphorescent probe reagent for detecting sulfadimidine and a preparation method thereof are disclosed, the reagent forms a supramolecular assembly by guest cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine and macrocyclic host cucurbit [8] urea in an aqueous solution, and the response of the assembly to the sulfadimidine is detected by utilizing room temperature phosphorescent emission. The preparation method comprises the following steps: performing amide condensation on chloroacetyl chloride and (1S, 2S) -1, 2-diaminocyclohexane to obtain an intermediate, reacting the intermediate with 4- (4-bromophenyl) -pyridine to form a salt, and assembling the obtained cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine and cucurbit [8] urea in water to obtain the supramolecular phosphorescence detection reagent. The water-soluble supramolecular phosphorescent probe reagent for detecting the sulfadimidine, provided by the invention, has a simple synthetic route; the detection of the sulfadimidine is efficient, rapid and high in sensitivity; the method can detect sulfadimidine in cells by a phosphorescence imaging method, and has wide biological application prospect.

Description

Supramolecular phosphorescent probe reagent for sulfadimidine detection and preparation method thereof
Technical Field
The invention relates to a preparation method of a novel supramolecular phosphorescent probe reagent for detecting sulfadimidine, which belongs to the field of antibiotic detection.
Background
Antibiotics refer to a class of secondary metabolites with anti-pathogen or other activities generated by microorganisms (including bacteria, fungi, actinomycetes) or higher animals and plants during life, and chemical substances capable of interfering with other life cell development functions. Sulfamethazine is an antibacterial sulfonamide antibiotic that blocks folate synthesis by inhibiting dihydrofolate synthase, which is an essential substance for bacteria to synthesize purines, thymidine, and deoxyribonucleic acid (DNA), thereby inhibiting bacterial growth. It is suitable for treating infection diseases such as hemolytic streptococcus, meningococcus, and pneumococcus. However, the long-term use of sulfadimidine can cause drug resistance of bacteria, and certain adverse reactions and toxic and side effects also exist on human bodies, including anaphylaxis, hemolytic anemia, liver and kidney injury, central nervous system toxicity and the like. It is therefore necessary to regulate its use by detection means, while spectroscopic analysis provides a sensitive detection method.
The spectroscopy identifies and detects molecules by converting molecule binding information into spectral signals which are easy to monitor, and the spectroscopy method with the characteristics of high sensitivity, high selectivity, instant responsiveness and the like has important significance. In recent years, supramolecular probes have been widely used in spectroscopic analysis and the like. The macrocyclic cucurbituril has a terminal carbonyl group and can be effectively bonded with cations, so that the macrocyclic cucurbituril is widely applied to various fields including molecular recognition, molecular assembly and the like. At present, many methods for detecting antibiotics have been widely reported, including carbon quantum dots, silicon quantum dots, polymer materials, and the like. However, these methods generally have the disadvantages of difficult preparation, high detection limit, long response time, difficult application to in vivo detection, and the like.
Disclosure of Invention
The invention aims to solve the problems in the prior art and provides the preparation of the supramolecular phosphorescent probe reagent with special responsiveness to the sulfadimidine, and the probe reagent has high sensitivity and simple preparation method and is suitable for the requirements of actual production and application.
The technical scheme of the invention is as follows:
a supramolecular phosphorescent probe reagent for sulfadimidine detection comprises a macrocyclic main body cucurbita [8]]The supermolecular assembly formed by two main and guest components in aqueous solution is used as a phosphorescence probe reagent, and effective room temperature phosphorescence is generated after the assembly, and the phosphorescence intensity has responsiveness to sulfadimidine. Cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine of formula C32H32Br2Cl2N4O2Structural formula is
Figure BDA0002819253220000021
A preparation method of a supramolecular phosphorescent probe reagent for detecting sulfadimidine comprises the following specific steps:
1) synthesis of intermediates
A solution of chloroacetyl chloride in dioxane was added to a solution of (1S, 2S) -1, 2-diaminocyclohexane and triethylamine in dioxane at 5 deg.C, after which the reaction mixture was stirred at room temperature for a period of time. The triethylamine hydrochloride formed was filtered off and the filtrate evaporated in vacuo to give a residue which was dissolved in dichloromethane. The resulting solution was then washed with water, 20% aqueous sodium carbonate solution and 0.5N hydrochloric acid, respectively. The organic phase was collected, concentrated and dried to give the intermediate solid product.
2) Synthesis of cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine
Dissolving the intermediate obtained in the step 1) and 4- (4-bromophenyl) -pyridine in an anhydrous N, N' -dimethylformamide solution, heating and refluxing to separate out a large amount of precipitates. After cooling, suction filtration is carried out, the solid is collected, washed by dichloromethane and ether and dried, and the product, namely the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine, is obtained.
3) Preparation of supramolecular phosphorescent probe reagent
Dissolving cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine and cucurbit [8] urea in water to prepare the supramolecular phosphorescent probe reagent for detecting sulfadimidine.
The mole ratio of the chloracetyl chloride, the (1S, 2S) -1, 2-diaminocyclohexane and the triethylamine is 2: 1: 2.
the concentration of chloroacetyl chloride in dioxane was 2 mol/L.
The concentration of the (1S, 2S) -1, 2-diaminocyclohexane in dioxane was 0.33 mol/L.
The concentration of the triethylamine in dioxane was 0.66 mol/L.
The volume ratio of the dichloromethane to the dioxane used for dissolving (1S, 2S) -1, 2-diaminocyclohexane is 2: 1.
the volume ratio of the washing water, 20% sodium carbonate aqueous solution, 0.5N hydrochloric acid and dichloromethane is 2: 2: 2: 1.
the molar ratio of the intermediate to 4- (4-bromophenyl) -pyridine is 1: 2.4.
the concentration of the intermediate in the anhydrous N, N' -dimethylformamide solution is 0.1 mol/L.
The volume ratio of the dichloromethane to the anhydrous N, N' -dimethylformamide solution is 5: 1.
The volume ratio of the diethyl ether to the anhydrous N, N' -dimethylformamide solution is 10: 1.
The molar ratio of the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine to cucurbit [8] urea is 1: 1.
The concentration of the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine in water was 10. mu. mol/L.
The invention has the advantages and beneficial effects that:
the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine prepared by the method has the advantages of simple synthetic route, mild reaction conditions, simple and convenient post-treatment, and suitability for amplification synthesis and practical production application; as a novel water-soluble supramolecular phosphorescent probe reagent for detecting sulfadimidine, the detection operation on the sulfadimidine is simple and practical, the detection reagent has high sensitivity and no destructiveness on a sample, and the identification result is displayed by a steady spectrum and is easy to monitor; the invention can also effectively detect sulfadimidine in living cells, and has wide application prospect.
Drawings
FIG. 1 is a schematic diagram of the synthetic route for cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine.
FIG. 2 is a steady state spectrum of the novel supramolecular phosphorescent probe reagent applied to sulfadimidine detection.
FIG. 3 is a fitting curve of the degree of quenching of the phosphorescence intensity in the steady-state spectrum of sulfadimidine detected by the supramolecular phosphorescent reagent and the concentration of sulfadimidine.
FIG. 4 shows the results of phosphorescent confocal experiments in 293T cells. Wherein, the three pictures (a), (b) and (c) are respectively a white light picture, a phosphorescence picture and an overlay picture of incubation only with the probe reagent; (d) the three pictures (e) and (f) are respectively a white light picture, a phosphorescence picture and an overlay picture of the co-incubation of the antibiotic and the probe reagent.
Detailed Description
Example 1:
1) synthesis of intermediates
1.13g (10mmol) of chloroacetyl chloride are dissolved in 5mL of dioxane at 5 ℃ and the solution is slowly added to a solution of 568mg (5mmol) of (1S, 2S) -1, 2-diaminocyclohexane and 1.4mL (10mmol) of triethylamine in 15mL of dioxane and the reaction mixture is stirred at room temperature for 2 hours. The triethylamine hydrochloride formed was filtered off and the filtrate evaporated in vacuo to give a residue which was dissolved in 30mL dichloromethane. The resulting solution was then washed with 60mL of water, 60mL of 20% aqueous sodium carbonate solution, and 60mL of 0.5N hydrochloric acid, respectively. The organic phase was collected, concentrated and dried to give the intermediate solid product.
2) Synthesis of cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine
267mg (1mmol) of the intermediate obtained in step 1) were dissolved in 561mg (2.4mmol) of 4- (4-bromophenyl) -pyridine in 10mL of anhydrous N, N' -dimethylformamide and reacted at 100 ℃ for 48 hours to precipitate a large amount of precipitate. After cooling, it was filtered with suction, and the solid was collected, washed with 50mL of dichloromethane, 100mL of ether, and dried to give the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine.
3) Preparation of supramolecular phosphorescent probes
7.35mg of cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine and 13.29mg of cucurbit [8] urea are dissolved in 1L of water to prepare the supramolecular phosphorescent probe reagent for detecting the sulfadimidine.
Example 2:
1) synthesis of intermediates
3.98g (35.2mmol) of chloroacetyl chloride are dissolved in 18mL of dioxane at 5 ℃, the solution is slowly added to a solution of 2g (17.6mmol) of (1S, 2S) -1, 2-diaminocyclohexane and 5mL (35.2mmol) of triethylamine in 55mL of dioxane, and the reaction mixture is stirred at room temperature for 3 hours. The triethylamine hydrochloride formed was filtered off and the filtrate evaporated in vacuo to give a residue which was dissolved in 100mL dichloromethane. The resulting solution was then washed with 200mL of water, 200mL of 20% aqueous sodium carbonate solution, and 200mL of 0.5N hydrochloric acid, respectively. The organic phase was collected, concentrated and dried to give the intermediate solid product.
2) Synthesis of cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine
475mg (1.8mmol) of the intermediate obtained in step 1) were dissolved in 18mL of anhydrous N, N' -dimethylformamide with 1g (4.3mmol) of 4- (4-bromophenyl) -pyridine and reacted at 110 ℃ for 36 hours to precipitate a large amount of precipitate. After cooling, it was filtered with suction, and the solid was collected, washed with 90mL of dichloromethane, 180mL of ether, and dried to give the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine.
3) Preparation of supramolecular phosphorescent probes
7.35mg of cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine and 13.29mg of cucurbit [8] urea are dissolved in 1L of water to prepare the supramolecular phosphorescent probe reagent for detecting the sulfadimidine.
Detection shows that the nuclear magnetism and high-resolution mass spectrum of the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine are characterized as follows:1H NMR(400MHz,DMSO-d6) δ 9.27(d, J ═ 5.6Hz,4H),8.75(s,2H),8.56(d, J ═ 6.3Hz,4H),8.04(d, J ═ 8.4Hz,4H),7.86(d, J ═ 8.2Hz,4H),5.93(d, J ═ 16.3Hz,2H),5.43(d, J ═ 16.0Hz,2H),3.62(s,2H),1.88(m,2H),1.68(m,2H),1.38(m,2H),1.25(m, 2H). HR-MS (ESI), calculated value C32H32Br2Cl2N4O2:[M-2Cl]2+331.0430, found 331.0435.
FIG. 1 is a schematic diagram of the synthetic route for cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine.
FIG. 2 is a steady state spectrum of sulfadimidine detected by the supramolecular phosphorescent reagent.
FIG. 3 is a fitting curve of the degree of quenching of the phosphorescence intensity in the steady-state spectrum of sulfadimidine detected by the supramolecular phosphorescent reagent and the concentration of sulfadimidine.
FIG. 4 shows the result of phosphorescence confocal imaging of 293T cells, as shown in the three images (a), (b) and (c) are respectively a white light image, a phosphorescence image and an overlay image of incubation with only the probe reagent. (d) The three pictures (e) and (f) are respectively a white light picture, a phosphorescence picture and an overlay picture of the co-incubation of the antibiotic and the probe reagent.
The specific application and effect of the invention are as follows:
7.35mg of cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine with 13.29mg of cucurbita [8]]Dissolving urea in 1L water to obtain 10-5M phosphorescent Probe reagent when 0.05-0.5 equivalent of Sulfamethazine is added to the SystemThe phosphorescence of the agent is gradually quenched. A curve can be fitted by the quenching degree of the phosphorescence intensity in the steady-state spectrum and the concentration of the sulfadimidine, and the curve is used for quantitatively analyzing the concentration of the sulfadimidine to be detected. And the detection limit of 1.86 multiplied by 10 can be obtained by fitting-7M, with a relatively high sensitivity.
293T cells are cultured in a culture medium for 24h, 10uM sulfadimidine solution is added into the 293T cells for culturing for 1h, then 10uM probe reagent is added into the 293T cells for culturing overnight, sulfadimidine solution is not added into a control group, and the recognition capability of the probe on the sulfadimidine in the cells is observed under a microscope. The results show that the cells previously treated with sulfadimidine solution exhibited phosphorescence quenching, while the cells not previously treated with sulfadimidine solution exhibited bright phosphorescence, as shown in figure 3, indicating that the phosphorescent probe was able to effectively detect sulfadimidine within the cells.

Claims (10)

1. A supramolecular phosphorescent probe reagent for sulfadimidine detection is characterized in that: bridging of 4- (4-bromophenyl) -pyridine with macrocyclic host cucurbita [8] by guest cyclohexanediamines]The supramolecular assembly formed by urea is used as a phosphorescent probe reagent, the molecular molar ratio of the supramolecular assembly to the phosphorescent probe reagent is 1:1, and the chemical formula of the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine is C32H32Br2Cl2N4O2Structural formula is
Figure FDA0003600494150000011
2. The method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 1, characterized in that it comprises the following steps:
1) synthesis of intermediates
Adding a solution of chloroacetyl chloride in dioxane to a solution of (1S, 2S) -1, 2-diaminocyclohexane and triethylamine in dioxane at 5 ℃ after which the reaction mixture is stirred at room temperature for 2-4 hours; the triethylamine hydrochloride formed is filtered off, the filtrate is evaporated in vacuo and the residue obtained is dissolved in dichloromethane; then washing the resulting solution with water, 20% sodium carbonate aqueous solution and 0.5N hydrochloric acid, respectively; concentrating and drying the organic phase to obtain an intermediate solid product;
2) synthesis of cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine
Dissolving the intermediate obtained in the step 1) and 4- (4-bromophenyl) -pyridine in an anhydrous N, N' -dimethylformamide solution, heating and refluxing to separate out a large amount of precipitate, cooling, performing suction filtration, collecting a solid, washing with dichloromethane and diethyl ether, and drying to obtain a product, namely the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine;
3) preparation of supramolecular phosphorescent probe reagent
Dissolving the obtained cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine and cucurbit [8] urea in water to prepare the supramolecular phosphorescent probe reagent for detecting the sulfadimidine.
3. The method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the mole ratio of the chloracetyl chloride, the (1S, 2S) -1, 2-diaminocyclohexane and the triethylamine is 2: 1: 2.
4. the method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the concentration of the chloracetyl chloride in the dioxane is 2 mol/L; the concentration of the (1S, 2S) -1, 2-diaminocyclohexane in dioxane is 0.33 mol/L; the concentration of the triethylamine in dioxane was 0.66 mol/L.
5. The method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the volume ratio of the dichloromethane to dioxane for dissolving (1S, 2S) -1, 2-diaminocyclohexane is 2: 1.
6. the method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the volume ratio of the washing water, the 20% sodium carbonate aqueous solution, the 0.5N hydrochloric acid and the dichloromethane is 2: 2: 2: 1.
7. the method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the molar ratio of the intermediate to 4- (4-bromophenyl) -pyridine is 1: 2.4.
8. the method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the concentration of the intermediate in the anhydrous N, N' -dimethylformamide solution is 0.1 mol/L.
9. The method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the volume ratio of the dichloromethane to the anhydrous N, N' -dimethylformamide solution is 5: 1; the volume ratio of the diethyl ether to the anhydrous N, N' -dimethylformamide solution is 10: 1.
10. The method for preparing the supramolecular phosphorescent probe reagent for sulfadimidine detection as claimed in claim 2, characterized in that: the molar ratio of the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine to cucurbit [8] urea is 1: 1; the concentration of the cyclohexanediamine bridged 4- (4-bromophenyl) -pyridine in water was 10. mu. mol/L.
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